Origin of the Reactivity of Allyl Chloride and a-Chloroacetaldehyde in SN2 Nucleophilic Substitution Reactions: A Theoretical Comparison

Robert D. Bach, Barry A. Coddens, Gregory J. Wolber

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

A comparison of the molecular orbitals of the transition state for the SN2 nucleophilic substitution of chloride ion on allyl chloride and a-chloroacetaldehyde was made by employing ab initio calculations. These data suggest that the enhanced rate of nucleophilic substitution for both reactions is the result of a low lying “allylic” bonding interaction present in the transition state. The origin of this relatively low lying molecular orbital is traced back to a three molecular orbital four-electron interaction between the nucelophile and the σ-π conjugated bonding and antibonding molecular orbitals comprising the σCCland σ*CClbonds of the substrate.

Original languageEnglish (US)
Pages (from-to)1030-1033
Number of pages4
JournalJournal of Organic Chemistry
Volume51
Issue number7
DOIs
StatePublished - Jan 1 1986

ASJC Scopus subject areas

  • Organic Chemistry

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